Stereoselective hydrogenation of (−)-menthone and (+)-isomenthone mixture using nickel catalysts

Stereoselective hydrogenation of (−)-menthone and (+)-isomenthone mixture using nickel catalysts The catalytic hydrogenation of an optically active mixture of (−)-menthone and (+)-isomenthone was studied. The catalysts Raney nickel and Ni/SiO2 were used for these hydrogenations. Catalysts modified with (2R,3R)-(+)-tartaric acid were tested as well. Various non-equilibrium mixtures of isomers were produced by means of these reactions, especially mixtures containing the less stable menthol isomers, (+)-neomenthol and (+)-neoisomenthol. (−)-Menthol was produced during these reactions to a limited extent, the production of (−)-isomenthol was barcly existent. Isomerization of (−)-menthone and (+)-isomenthone occurred during these reactions. Isomerizations among individual isomers were barely detectable. The catalysts used showed a very low activity under the given reaction conditions. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Research on Chemical Intermediates Springer Journals

Stereoselective hydrogenation of (−)-menthone and (+)-isomenthone mixture using nickel catalysts

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Publisher
Brill Academic Publishers
Copyright
Copyright © 2000 by VSP
Subject
Chemistry; Catalysis; Physical Chemistry; Inorganic Chemistry
ISSN
0922-6168
eISSN
1568-5675
D.O.I.
10.1163/156856700X00390
Publisher site
See Article on Publisher Site

Abstract

The catalytic hydrogenation of an optically active mixture of (−)-menthone and (+)-isomenthone was studied. The catalysts Raney nickel and Ni/SiO2 were used for these hydrogenations. Catalysts modified with (2R,3R)-(+)-tartaric acid were tested as well. Various non-equilibrium mixtures of isomers were produced by means of these reactions, especially mixtures containing the less stable menthol isomers, (+)-neomenthol and (+)-neoisomenthol. (−)-Menthol was produced during these reactions to a limited extent, the production of (−)-isomenthol was barcly existent. Isomerization of (−)-menthone and (+)-isomenthone occurred during these reactions. Isomerizations among individual isomers were barely detectable. The catalysts used showed a very low activity under the given reaction conditions.

Journal

Research on Chemical IntermediatesSpringer Journals

Published: Jan 1, 2000

References

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